O-Toluidine → N-(2-Methylphenyl)butanimidic acid

HRID 1168005Notes

Reaction equation

[C:1]([NH:6][C:7]1[CH:16]=[CH:15][C:10](C(OC)=O)=[CH:9][C:8]=1[CH3:17])(=[O:5])[CH2:2][CH2:3][CH3:4].NC1C(C)=CC=CC=1.C(Cl)(=O)CCC>>[C:1]([NH:6][C:7]1[CH:16]=[CH:15][CH:10]=[CH:9][C:8]=1[CH3:17])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

Reactant 3

HCID 7242O-Toluidine

HCID 8855Butyryl chloride

HCID 9856104Methyl 4-butyramido-3-methylbenzoate

Product 1

HCID 221809N-(2-Methylphenyl)butanimidic acid

Procedure

A process for preparing methyl N-butyryl-4-amino-3-methyl-benzoate, comprising a first step of reacting o-toluidine with butyryl chloride to give N-butyryl-2-methylaniline, a second step of brominating the N-butyryl-2-methylaniline to give N-(4-bromo-2-methylphenyl)butanamide and a third step of converting the N-(4-bromo-2-methylphenyl)butanamide by reaction with carbon monoxide and methanol in the presence of a palladium catalyst to give methyl N-butyryl-4-amino-3-methylbenzoate.

Sources & evidence

ORD record: ord-1ec961f125064e59a6ad2022568e0d01
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06620962B2

Reaction notes

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